HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl Salicylate → 2-(2-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-cyclopropyl-methoxy-ethoxy)-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl Salicylate | HCID 4133 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | 2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-cyclopropyl methoxy-ethanol | HCID 86720735 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(2-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-cyclopropyl-methoxy-ethoxy)-benzoic acid methyl ester | HCID 131733278 | 9.7% |
Reaction Steps
To a suspension of ether-alcohol 44 (0.9 g, 0.0024 mol) in THF (5 ml) was added triphenyl phosphene (0.93 g, 0.0035 mol) and methyl salicylate (0.54 ml, 0.0036 mol). The resulting mixture was stirred at ambient temperature for 5 minutes and diisopropyl azodicarboxilate (0.71 g, 0.0035 mol) was added drop wise to the mixture. The reaction mixture was stirred at the same temperature for seven days. Dichloromethane (30 ml) was added to the mixture followed by drying of the resulted solution over sodium sulfate, evaporation of the solvents and FC to give ester 45 (0.12 g, 9.62%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09102665B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-b7039e9b02744d678f858c9add7671f1 |
| Source note | uspto-grants-2015_08 |